2,3-trans-Flav-3-ene epoxide reacts with phenol to give 2,3-trans-3,4-cis-4-phenoxyflavan-3-ol and with sodium phenoxide to give 2,3-trans-3,4-trans-4-phenoxy-flavan-3-ol, both compounds being stereochemically pure and both resulting in good yield.
B. R. Brown and M. R. Shaw, J. Chem. Soc. D, 1971, 1579a DOI: 10.1039/C2971001579A
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